A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Book Winchester Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Winchester bed & breakfast

Exterior

1. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (97 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
$319 nightly
The price is $368
Aug 11 - Aug 12
Total with taxes and fees
Glen Gordon Manor
Front of property

2. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (687 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
$161 nightly
The price is $177
Aug 12 - Aug 13
Total with taxes and fees
Hillbrook Inn
Reception

3. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (318 reviews)
"Wonderful stay at a beautiful spot."
United States
michael
$146 nightly
The price is $167
Sep 2 - Sep 3
Total with taxes and fees
Loudoun Valley Manor
Reception

4. Light Horse Inn

Light Horse Inn
2.0 star property
Harpers Ferry
9.4 out of 10, Exceptional, (135 reviews)
"This is a very nice and relaxing inn with very helpful staff"
United States
David
$165 nightly
The price is $177
Aug 13 - Aug 14
Total with taxes and fees
Light Horse Inn
Exterior

5. Cantuta Inn

Cantuta Inn
3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (78 reviews)
"Clean, great location, courteous staff. Could not ask for better."
United States
Anthony
$135 nightly
The price is $151
Aug 9 - Aug 10
Total with taxes and fees
Cantuta Inn
Interior

6. Light Horse Inn: Suite 2

Light Horse Inn: Suite 2
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay. Staff exceptionally friendly"
United States
Michael
$194 nightly
The price is $240
Aug 13 - Aug 14
Total with taxes and fees
Light Horse Inn: Suite 2
Interior

7. Light Horse Inn: Suite 6

Light Horse Inn: Suite 6
Bolivar
9.8 out of 10, Exceptional, (8 reviews)
"Great spot!"
United States
Theresa
$197 nightly
The price is $222
Aug 6 - Aug 7
Total with taxes and fees
Light Horse Inn: Suite 6
Front of property

8. Stone Manor Boutique Inn

Stone Manor Boutique Inn
3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (109 reviews)
"Lovely inn in beautiful setting."
United States
Linda
$259 nightly
The price is $295
Aug 6 - Aug 7
Total with taxes and fees
Stone Manor Boutique Inn
Interior

9. Light Horse Inn: Suite 4

Light Horse Inn: Suite 4
Harpers Ferry
10.0 out of 10, Exceptional, (13 reviews)
"It was an historic building with many charming features. Breakfasts served were good and the chefs were very ice."
United States
Caryl R.
$211 nightly
The price is $237
Aug 10 - Aug 11
Total with taxes and fees
Light Horse Inn: Suite 4
Exterior

10. Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete."
United States
Daniel F.
$295 nightly
The price is $327
Aug 11 - Aug 12
Total with taxes and fees
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Porch

11. Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
$359 nightly
The price is $387
Aug 6 - Aug 7
Total with taxes and fees
Gay Street Inn
Front of property

12. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (453 reviews)
"Amazing place with incredible history!"
United States
Andrea
$155 nightly
The price is $176
Aug 6 - Aug 7
Total with taxes and fees
The Carriage Inn B&B
Hallway

13. Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (138 reviews)
"Beautiful historic inn! Gorgeous property and close to everything! Can’t wait to visit again."
United States
Kristine
$258 nightly
The price is $294
Aug 9 - Aug 10
Total with taxes and fees
Inn at Evergreen
Garden

14. Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
9.8 out of 10, Exceptional, (37 reviews)
"Staff was wonderful and caring! Breakfast was delicious. The tavern had wonderful beer and we enjoyed meeting Norman the beagle."
United States
Deborah
$296 nightly
The price is $341
Aug 10 - Aug 11
Total with taxes and fees
Hopkins Ordinary Bed Breakfast and Ale Works
Outdoor dining

15. Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (38 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
$423 nightly
The price is $482
Aug 6 - Aug 7
Total with taxes and fees
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Outdoor dining

16. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (70 reviews)
"What a lovely place. Quiet and very prettyLots of good recommendations for the Lica areaWe’ll likely be back"
United States
Tom W.
$367 nightly
The price is $418
Aug 6 - Aug 7
Total with taxes and fees
The Van Gogh Room in Villa
Exterior

17. Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
10.0 out of 10, Exceptional, (1 review)
"Great weekend getaway for my birthday that happened to fall on the 4 th of July weekend . Accommodations were amazing and it was hard to leave . Got a lot of well spent alone time and enjoyed sine wineries around the area !"
United States
Lorine H.
$316 nightly
The price is $360
Aug 12 - Aug 13
Total with taxes and fees
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Interior

18. Light Horse Inn: Suite 7

Light Horse Inn: Suite 7
Bolivar
9.6 out of 10, Exceptional, (7 reviews)
"The property was well-kept, and breakfast was delicious with friendly staff and guests."
United States
Rebecca
$197 nightly
The price is $222
Aug 6 - Aug 7
Total with taxes and fees
Light Horse Inn: Suite 7
Interior entrance

19. The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (10 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
$631 nightly
The price is $719
Aug 14 - Aug 15
Total with taxes and fees
The Inn at Grass Roots Hill
Exterior

20. Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lovettsville
10.0 out of 10, Exceptional, (1 review)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
$12,943 nightly
The price is $15,330
Aug 6 - Aug 7
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Skyland

Skyland

10/10 Excellent
"Staff were friendly. The room was very nice. The view was gorgeous. This place was right in the middle of many hiking trails. Please visit the meadows if you come to Shenandoah National park!"
Stefanie 3-night trip
Posted 3 hours ago
Skyland

Find out more about Winchester

Winchester B&B information

Number of reviews
1,419
Accommodation
47 B&B
Lowest Price
$151
Highest Price
$15,330

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $151 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winchester?
The best time to book a B&B in Winchester is during the vibrant fall months of September and October. This period attracts travelers looking to experience the stunning autumn foliage and partake in various local events, all while enjoying the comfortable temperatures ranging from the mid-50s to low 70s Fahrenheit. The scenery is particularly enchanting as the leaves change, creating a picturesque backdrop for outdoor activities such as hiking the nearby trails or exploring the charming downtown area.

September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine.

For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter.
What is the difference between a Winchester Bed & Breakfast and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

Explore a world of travel with Expedia